engleski

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4- carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

1, 2, 3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1, 2, 3-triazole moiety. In this work, a one-step multigram scale synthesis of 4- formyl-1-(4-nitrophenyl)-1H-1, 2, 3-triazole (FNPT) as a preferred reagent for the synthesis of 1- alkyl-4-formyltriazoles is described, making use of the commercially available 3- dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl- 1, 2, 3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

1, 2, 3-triazole ; aldehyde ; cycloaddition ; enamine ; Cornforth ; rearrangement ; amines ; metal-free

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